Pyrimidines

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.149849-92-3, name is 2-Chloropyrimidine-4-carboxylic acid, molecular formula is C5H3ClN2O2, molecular weight is 158.54, as common compound, the synthetic route is as follows.149849-92-3

To a solution of 2-chloropyrimidine-4-carboxylic acid (1.00 g, 6.3 mmol) in anhydrousDCM (15 mL) were added oxalyl chloride (1.1 mL, 12.6 mmol) and DMF (0.1 mL) dropwise at0 C. The mixture was stirred at rt for 2 hours, and then cooled to 0 C. To the mixture were added triethylamine (1.28 mL, 9.5 mmol) and a solution of methylamine in THF (2M, 3.47 mL, 6.9 mmol) slowly at 0 C. The reaction mixture was stirred at rt for 12 hours, and then quenched with water (25 mL). The separated organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 2/1) to give the title compound as a white solid (1.06 g, 98.1%). The compound was characterized by the following spectroscopic data:LC-MS (ESI, pos. ion) m/z: 172.2 [M + H] .

Statistics shows that 149849-92-3 is playing an increasingly important role. we look forward to future research findings about 2-Chloropyrimidine-4-carboxylic acid.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; CHENG, Changchung; WO2015/169180; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 51752-67-1, name is 4-Chloropyrido[3,4-d]pyrimidine, the common compound, a new synthetic route is introduced below. 51752-67-1

EXAMPLE 24 (3-Ethynyl-phenyl)-pyrido[3,4d]pyrimidin4-yl-amine To 4-chloro-pyrido[3,4-d]pyrimidine (250 mg, 1.50 mmol) in N-methylpyrrolidin-2-one (0.5 mL) was added 3-ethynylaniline (212 mg, 1.81 mmol) and pyridine (237 mg, 3.0 mmol). The mixture was heated to 80 C. under an atmosphere of dry N2(g) for 3 hours. The reaction mixture was dissolved in CHCl3 and washed with saturated aqueous Na2CO3, and brine. The organic phase was dried over Na2SO4, concentrated in vacuo, and flash chromatographed on silica with a gradient of 40% to 70% acetone/hexanes to afford 120 mg of product. This material was precipitated as its hydrochloride salt by dissolution in minimal CHCl3, titration with HCl (1 eq.) in diethyl ether, and dilution with diethyl ether.

The synthetic route of 51752-67-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARNOLD, LEE DANIEL; MOYER, MIKEL PAUL; SOBOLOV-JAYNES, SUSAN BETH; US2002/45630; (2002); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

45588-79-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 45588-79-2, name is 4-(Aminomethyl)pyrimidine. A new synthetic method of this compound is introduced below.

To a stirred solution of 4-(cis-8-(dimethylamino)-3-oxo-8-phenyl-2-azaspiro[4. 5]decan-2- yI)-2,2-dimethylbutanoic acid hydrochloride (300mg, 0.71 mmol) in THF(1 0mL), diisopropylethylamine (490mg, 3.8Ommol) and HATU (541mg, 1 .43mmol) were added at RT. The reaction mixture was stirred at RT for 45mm and then pyrimidin-4-yl- methanamine (114mg, 1 .O45mmol) was added at 0C. The reaction mixture was warmedto RT and stirred for 16h. The reaction mixture was quenched with saturated NaHCO3 Solution, extracted with 10%methanol in DCM (3X25mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude compound. Purification by column chromatography over silica gel (100-200 mesh) by using 1 0%methanol in DCM with traces of ammonia as eluent to give 160mg ofcompound which was further purified by preparative TLC by using 5% methanol in DCM as mobile phase to give 110 mg (33%) of cis- 4-(8-Dimethylamino-3-oxo-8-phenyl-2- azaspiro[4.5]decan-2-yl)-2,2-dimethyl-N-(pyrimidin-4-yl-methyl)-butyramide as solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 45588-79-2, 4-(Aminomethyl)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; WEGERT, Anita; KUeHNERT, Sven; KOENIGS, Rene, Michael; NOLTE, Bert; LINZ, Klaus; HARLFINGER, Stephanie; KOeGEL, Babette-Yvonne; RATCLIFFE, Paul; THEIL, Fritz; GROeGER, Olga; BRAUN, Birgit; (223 pag.)WO2016/8582; (2016); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 60025-09-4, name is 4-Amino-6-chloropyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. 60025-09-4

4- Amino-6-(((lS, lR)-l-(3-(2-pyridinyl)-l,6-naphthyridin-2-yl)ethyl)amino)-5- pyrimidinecarbonitrile; To a stirred solution of l-(3-(pyridin-2-yl)-l,6-naphthyridin-2-yl)ethanamine (15 mg, 0.060 mmol) in butanol (1.5 mL) was added 4-amino-6-chloropyrimidine-5- carbonitrile (9.26 mg, 0.060 mmol) and N-ethyl-N-isopropylpropan-2-amine (20.9 uL, 0.120 mmol). The reaction was heated at 120 C for 2 h. After this time the reaction was cooled to r.t. The resulting precipitate was filtered and washed with hexanes to give racemic 4-amino-6-(((lS, lR)-l-(3-(2-pyridinyl)-l,6- naphthyridin-2-yl)ethyl)amino)-5-pyrimidinecarbonitrile. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 9.33 (1 H, s), 8.83 (2 H, d, J=5.9 Hz), 8.33 (1 H, s), 8.14 (1 H, s), 8.02 (1 H, d, J=5.9 Hz), 7.93 (1 H, td, J=7.7, 1.8 Hz), 7.64 (2 H, d, J=7.8 Hz), 7.44 (1 H, ddd, J=7.6, 4.9, 1.0 Hz), 6.15 (1H, m), 5.28 (2 H, bs), 1.38 – 1.43 (3 H, m). Mass Spectrum (ESI) m/e = 251.0. Mass Spectrum (ESI) m/e = 369.2 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60025-09-4, 4-Amino-6-chloropyrimidine-5-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; CHEN, Yi; CUSHING, Timothy, D.; FISHER, Benjamin; GONZALEZ LOPEZ DE TURISO, Felix; HAO, Xiaolin; SHIN, Youngsook; WO2012/87784; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

63200-54-4, Adding a certain compound to certain chemical reactions, such as: 63200-54-4, 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 63200-54-4, blongs to pyrimidines compound.

2-Chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-Patent; VALEANT RESEARCH & DEVELOPMENT; WO2006/122003; (2006); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

2435-50-9 ,Some common heterocyclic compound, 2435-50-9, molecular formula is C5H4N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: SI, Figure 4. General procedure of the reductive amination reactions: synthesis of AA9-AA24 compounds (Tables 1 and 2). The ethyl 3-amino-4-(cyclohexylamino)benzoate (AA1) and derivatives (1 equiv.)and benzaldehyde (1 equiv) were heated in DCE for 1h at 80 oC in the presence of molecular sieves (4 A), then the mixture was cooled down to room temperature before addition of the NaBH(OAc)3 (1.6 equiv.) in small portions over 3h. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 17h. The reaction mixture was quenched with aqueous saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM: MeOH (50:1), to provide the desired AA9-AA24 compounds (Tables 1-2).

According to the analysis of related databases, 2435-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iniguez, Eva A.; Perez, Andrea; Maldonado, Rosa A.; Skouta, Rachid; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5315 – 5320;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia